1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(naphthalen-1-ylsulfanylmethyl)pyrimidine-2,4-dione

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(naphthalen-1-ylsulfanylmethyl)pyrimidine-2,4-dione
• 化学式: C₂₀H₂₀N₂O₅S
• 分子量: 400.455
• InChiKey: GBZMHGGBGYTDLM-LZLYRXPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(naphthalen-1-ylsulfanylmethyl)pyrimidine-2,4-dione
  参考文献：
  名称：

  A new synthetic analogue of thymidine, 7-(3-bromo-phenoxy)-thymidine, inhibits the proliferation of tumor cells

  摘要：

  Modified thymidine analogues have been highlighted as useful agents for the treatment of cancer and viral diseases due to their potent biological activities. In the present study, we synthesized a new thymidine analogue, 7-(3-bromo-phenoxy)-thymidine (4a), as a potential lead for anti-tumor agent. Compound 4a potently inhibits HeLa cell proliferation with an IC50 of 15 muM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.039

文献信息

• A new synthetic analogue of thymidine, 7-(3-bromo-phenoxy)-thymidine, inhibits the proliferation of tumor cells
  作者：Kyung Noo Kim、Jiyong Lee、Dong Hoon Kim、Jong-Shin Yoo、Ho Jeong Kwon

  DOI：10.1016/j.bmcl.2004.10.039

  日期：2005.1

  Modified thymidine analogues have been highlighted as useful agents for the treatment of cancer and viral diseases due to their potent biological activities. In the present study, we synthesized a new thymidine analogue, 7-(3-bromo-phenoxy)-thymidine (4a), as a potential lead for anti-tumor agent. Compound 4a potently inhibits HeLa cell proliferation with an IC50 of 15 muM. (C) 2004 Elsevier Ltd. All rights reserved.